NPASS Compound

Structure

CID61004 OpenBabel06191715392D 104106 0 0 1 0 0 0 0 0999 V2000 2.5738 -2.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8517 7.7476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3214 9.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8579 -1.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5738 -1.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5793 5.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5793 4.9533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7214 6.4393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0726 -1.1912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7214 4.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 5.9439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5679 -0.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4976 5.5035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6457 6.7786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2338 4.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3819 6.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7334 11.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 3.4673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4072 3.9222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1555 3.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1476 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9393 12.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7214 2.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2013 2.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0505 4.6357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 0.4953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1036 -0.9852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1733 8.1044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 4.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9673 7.1354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1476 7.9252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2897 9.4112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1155 8.4105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7159 -0.9907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8635 4.9533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7035 6.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1759 5.1467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1476 2.9720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6711 4.5851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5807 3.0038 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2897 0.4953 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7912 11.0114 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4371 8.7672 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1476 4.9533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0252 6.8292 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2897 7.4299 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9050 0.4029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8815 12.5926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 8.9159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7214 1.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9375 2.2903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6857 5.2986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 7.4299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7159 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1476 1.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5229 3.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8770 5.5541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6431 9.7362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2897 4.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2890 7.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2897 6.4393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1110 1.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8579 0.4953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0550 11.6743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2897 10.4019 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6177 11.9298 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 7.9252 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7289 4.2790 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2897 1.4860 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2897 3.4673 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3748 2.0348 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5852 10.0424 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4949 8.4611 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8192 5.8602 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1476 5.9439 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5738 0.4953 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.9121 4.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0875 13.5617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5738 9.4112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5793 0.9907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 0.9907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7315 1.3213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8796 2.5965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6279 4.9925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4797 6.2676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 -0.9907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7214 0.4953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8635 7.9252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 6.4393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0055 1.4860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2591 2.6471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1408 6.2170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 -0.9907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9069 10.3991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 4.9533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3468 7.1860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 5.9439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0531 1.6781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8579 1.4860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2610 12.6433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1128 11.3681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 33 1 0 0 0 0 3 33 1 0 0 0 0 5 34 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 9 27 1 0 0 0 0 10 35 2 0 0 0 0 11 35 1 0 0 0 0 12 47 1 0 0 0 0 13 15 1 0 0 0 0 13 36 2 0 0 0 0 14 16 2 0 0 0 0 14 36 1 0 0 0 0 15 37 2 0 0 0 0 16 37 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 48 1 0 0 0 0 23 50 1 0 0 0 0 24 51 1 0 0 0 0 25 52 1 0 0 0 0 26 53 1 0 0 0 0 27 79 1 0 0 0 0 28 33 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 54 1 0 0 0 0 32 49 1 0 0 0 0 32 67 1 0 0 0 0 34 4 1 6 0 0 0 34 55 1 0 0 0 0 37 80 1 0 0 0 0 38 18 1 1 0 0 0 38 56 1 0 0 0 0 38 72 1 0 0 0 0 39 19 1 1 0 0 0 39 58 1 0 0 0 0 39 70 1 0 0 0 0 40 20 1 6 0 0 0 40 57 1 0 0 0 0 40 73 1 0 0 0 0 41 21 1 1 0 0 0 41 59 1 0 0 0 0 41 71 1 0 0 0 0 42 17 1 1 0 0 0 42 66 1 0 0 0 0 42 74 1 0 0 0 0 43 28 1 1 0 0 0 43 60 1 0 0 0 0 43 75 1 0 0 0 0 44 29 1 1 0 0 0 44 61 1 0 0 0 0 44 77 1 0 0 0 0 45 30 1 1 0 0 0 45 62 1 0 0 0 0 45 76 1 0 0 0 0 46 31 1 1 0 0 0 46 63 1 0 0 0 0 46 69 1 0 0 0 0 47 64 1 1 0 0 0 47 79 1 0 0 0 0 48 68 2 0 0 0 0 48 81 1 0 0 0 0 49 69 2 3 0 0 0 49 82 1 0 0 0 0 50 83 2 0 0 0 0 50 84 1 0 0 0 0 51 85 2 0 0 0 0 51 86 1 0 0 0 0 52 87 2 0 0 0 0 52 88 1 0 0 0 0 53 89 2 0 0 0 0 53 90 1 0 0 0 0 54 91 2 0 0 0 0 54 92 1 0 0 0 0 55 65 1 1 0 0 0 55 78 1 0 0 0 0 56 71 2 3 0 0 0 56 93 1 0 0 0 0 57 70 2 3 0 0 0 57 94 1 0 0 0 0 58 76 2 3 0 0 0 58 95 1 0 0 0 0 59 78 2 3 0 0 0 59 96 1 0 0 0 0 60 74 2 3 0 0 0 60 97 1 0 0 0 0 61 72 2 3 0 0 0 61 98 1 0 0 0 0 62 75 2 3 0 0 0 62 99 1 0 0 0 0 63 77 2 3 0 0 0 63100 1 0 0 0 0 64 73 2 3 0 0 0 64101 1 0 0 0 0 65 79 1 0 0 0 0 65102 2 0 0 0 0 66103 2 0 0 0 0 66104 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1467.64
Volume:	1423.861
LogP:	-0.311
LogD:	5.244
LogS:	-1.544
# Rotatable Bonds:	51
TPSA:	649.87
# H-Bond Aceptor:	38
# H-Bond Donor:	21
# Rings:	3
# Heavy Atoms:	38

MedChem Properties

QED Drug-Likeness Score:	0.033
Synthetic Accessibility Score:	7.373
Fsp3:	0.545
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.059
MDCK Permeability:	0.0006673178286291659
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.898
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	35.97991943359375%
Volume Distribution (VD):	0.955
Pgp-substrate:	42.52996826171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.525
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.639
Skin Sensitization:	0.669
Carcinogencity:	0.274
Eye Corrosion:	0.717
Eye Irritation:	0.065
Respiratory Toxicity:	0.969

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC61004

Natural Product ID:	NPC61004
*Common Name:**	Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-Gln
IUPAC Name:	(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbonyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
Synonyms:
Standard InCHIKey:	ZNEKMMIWGPUTGR-SQJOKQRMSA-N
Standard InCHI:	InChI=1S/C66H93N13O25/c1-5-34(4)55(78-59(96)41(21-26-53(89)90)71-56(93)38(18-23-50(83)84)72-61(98)44(29-35-10-7-6-8-11-35)77-63(100)46(31-54(91)92)69-49(82)32-67)65(102)79-27-9-12-47(79)64(101)73-40(20-25-52(87)88)57(94)70-39(19-24-51(85)86)58(95)76-45(30-36-13-15-37(80)16-14-36)62(99)75-43(28-33(2)3)60(97)74-42(66(103)104)17-22-48(68)81/h6-8,10-11,13-16,33-34,38-47,55,80H,5,9,12,17-32,67H2,1-4H3,(H2,68,81)(H,69,82)(H,70,94)(H,71,93)(H,72,98)(H,73,101)(H,74,97)(H,75,99)(H,76,95)(H,77,100)(H,78,96)(H,83,84)(H,85,86)(H,87,88)(H,89,90)(H,91,92)(H,103,104)/t34-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,55-/m0/s1
SMILES:	CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=N[C@@H](CCC(=O)O)C(=N[C@@H](CCC(=O)O)C(=N[C@@H](Cc1ccc(cc1)O)C(=N[C@@H](CC(C)C)C(=N[C@@H](CCC(=N)O)C(=O)O)O)O)O)O)O)N=C([C@H](CCC(=O)O)N=C([C@H](CCC(=O)O)N=C([C@H](Cc1ccccc1)N=C([C@H](CC(=O)O)N=C(CN)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL411059
PubChem CID:	16138839
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0003297] Organic Polymers [CHEMONTID:0003298] Polypeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518.1	Gardenia jasminoides var. grandiflora	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3700.0	nM	PMID[573273]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC61004 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1057
0.2-0.3	5378
0.3-0.4	11906
0.4-0.5	16303
0.5-0.6	6643
0.6-0.7	794
0.7-0.8	277
0.8-0.85	93
0.85-0.9	28
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8954	High Similarity	NPC56685
0.8931	High Similarity	NPC328649
0.8889	High Similarity	NPC471165
0.8797	High Similarity	NPC241794
0.879	High Similarity	NPC244336
0.875	High Similarity	NPC16188
0.8726	High Similarity	NPC326349
0.8726	High Similarity	NPC323336
0.871	High Similarity	NPC202198
0.8704	High Similarity	NPC475204
0.8704	High Similarity	NPC475123
0.8667	High Similarity	NPC476989
0.8623	High Similarity	NPC477637
0.8599	High Similarity	NPC244509
0.8589	High Similarity	NPC46009
0.8589	High Similarity	NPC40234
0.8581	High Similarity	NPC473491
0.8506	High Similarity	NPC477638
0.8506	High Similarity	NPC477632
0.8494	Intermediate Similarity	NPC50016
0.8485	Intermediate Similarity	NPC137627
0.8485	Intermediate Similarity	NPC306804
0.8466	Intermediate Similarity	NPC294516
0.8466	Intermediate Similarity	NPC107938
0.8457	Intermediate Similarity	NPC63931
0.8424	Intermediate Similarity	NPC328494
0.8408	Intermediate Similarity	NPC233702
0.8385	Intermediate Similarity	NPC469243
0.8373	Intermediate Similarity	NPC273755
0.8373	Intermediate Similarity	NPC475532
0.8364	Intermediate Similarity	NPC198254
0.8364	Intermediate Similarity	NPC274198
0.8354	Intermediate Similarity	NPC261934
0.8354	Intermediate Similarity	NPC5194
0.8323	Intermediate Similarity	NPC473402
0.8323	Intermediate Similarity	NPC26108
0.8323	Intermediate Similarity	NPC165285
0.8323	Intermediate Similarity	NPC476227
0.8313	Intermediate Similarity	NPC230611
0.8313	Intermediate Similarity	NPC89831
0.8284	Intermediate Similarity	NPC269750
0.8284	Intermediate Similarity	NPC45037
0.8284	Intermediate Similarity	NPC194671
0.8276	Intermediate Similarity	NPC61332
0.8276	Intermediate Similarity	NPC240130
0.8272	Intermediate Similarity	NPC475544
0.8253	Intermediate Similarity	NPC276506
0.825	Intermediate Similarity	NPC476268
0.8239	Intermediate Similarity	NPC262166
0.8232	Intermediate Similarity	NPC223207
0.8214	Intermediate Similarity	NPC155506
0.8214	Intermediate Similarity	NPC159767
0.8193	Intermediate Similarity	NPC129486
0.8187	Intermediate Similarity	NPC473404
0.8182	Intermediate Similarity	NPC471771
0.8182	Intermediate Similarity	NPC290755
0.8182	Intermediate Similarity	NPC477631
0.8182	Intermediate Similarity	NPC304074
0.8171	Intermediate Similarity	NPC477636
0.8166	Intermediate Similarity	NPC196243
0.8155	Intermediate Similarity	NPC248670
0.8137	Intermediate Similarity	NPC473580
0.8133	Intermediate Similarity	NPC302597
0.8133	Intermediate Similarity	NPC141957
0.8129	Intermediate Similarity	NPC475564
0.8129	Intermediate Similarity	NPC170302
0.8129	Intermediate Similarity	NPC475409
0.8107	Intermediate Similarity	NPC17698
0.8107	Intermediate Similarity	NPC279871
0.8079	Intermediate Similarity	NPC326966
0.8052	Intermediate Similarity	NPC313694
0.8052	Intermediate Similarity	NPC242159
0.8045	Intermediate Similarity	NPC477639
0.8012	Intermediate Similarity	NPC473546
0.8	Intermediate Similarity	NPC136797
0.8	Intermediate Similarity	NPC473354
0.8	Intermediate Similarity	NPC158277
0.7976	Intermediate Similarity	NPC280022
0.7955	Intermediate Similarity	NPC94862
0.7919	Intermediate Similarity	NPC153554
0.7874	Intermediate Similarity	NPC476321
0.7862	Intermediate Similarity	NPC81026
0.7861	Intermediate Similarity	NPC97526
0.7861	Intermediate Similarity	NPC119652
0.7853	Intermediate Similarity	NPC39431
0.7829	Intermediate Similarity	NPC471526
0.7809	Intermediate Similarity	NPC102959
0.7799	Intermediate Similarity	NPC266741
0.7784	Intermediate Similarity	NPC294951
0.7772	Intermediate Similarity	NPC477551
0.7765	Intermediate Similarity	NPC60516
0.7751	Intermediate Similarity	NPC254700
0.7747	Intermediate Similarity	NPC329295
0.7735	Intermediate Similarity	NPC302715
0.7712	Intermediate Similarity	NPC325651
0.7706	Intermediate Similarity	NPC209463
0.7692	Intermediate Similarity	NPC472923
0.7684	Intermediate Similarity	NPC471050
0.7684	Intermediate Similarity	NPC471048
0.7684	Intermediate Similarity	NPC471049
0.7673	Intermediate Similarity	NPC91953
0.7667	Intermediate Similarity	NPC473305
0.7667	Intermediate Similarity	NPC163961
0.7665	Intermediate Similarity	NPC287757
0.7665	Intermediate Similarity	NPC319320
0.7663	Intermediate Similarity	NPC477552
0.7663	Intermediate Similarity	NPC477550
0.7661	Intermediate Similarity	NPC186617
0.764	Intermediate Similarity	NPC299806
0.7637	Intermediate Similarity	NPC65714
0.7633	Intermediate Similarity	NPC133470
0.7633	Intermediate Similarity	NPC289776
0.7633	Intermediate Similarity	NPC191863
0.7616	Intermediate Similarity	NPC473693
0.7616	Intermediate Similarity	NPC471568
0.761	Intermediate Similarity	NPC197921
0.7576	Intermediate Similarity	NPC122590
0.7576	Intermediate Similarity	NPC473341
0.7564	Intermediate Similarity	NPC244866
0.7562	Intermediate Similarity	NPC469360
0.7562	Intermediate Similarity	NPC77905
0.7561	Intermediate Similarity	NPC475168
0.7561	Intermediate Similarity	NPC7817
0.7557	Intermediate Similarity	NPC475421
0.7554	Intermediate Similarity	NPC473371
0.7548	Intermediate Similarity	NPC255447
0.7541	Intermediate Similarity	NPC328763
0.753	Intermediate Similarity	NPC470902
0.7527	Intermediate Similarity	NPC473378
0.7527	Intermediate Similarity	NPC473407
0.7514	Intermediate Similarity	NPC471592
0.7514	Intermediate Similarity	NPC234069
0.75	Intermediate Similarity	NPC257390
0.7486	Intermediate Similarity	NPC477462
0.7485	Intermediate Similarity	NPC311658
0.7473	Intermediate Similarity	NPC174122
0.7473	Intermediate Similarity	NPC64140
0.7469	Intermediate Similarity	NPC209509
0.7455	Intermediate Similarity	NPC324081
0.7444	Intermediate Similarity	NPC138083
0.7438	Intermediate Similarity	NPC48202
0.7432	Intermediate Similarity	NPC248822
0.743	Intermediate Similarity	NPC470903
0.743	Intermediate Similarity	NPC167763
0.743	Intermediate Similarity	NPC470112
0.7421	Intermediate Similarity	NPC471264
0.7421	Intermediate Similarity	NPC471265
0.7419	Intermediate Similarity	NPC111428
0.7399	Intermediate Similarity	NPC473502
0.7394	Intermediate Similarity	NPC2501
0.738	Intermediate Similarity	NPC323662
0.7372	Intermediate Similarity	NPC478147
0.7368	Intermediate Similarity	NPC27581
0.7363	Intermediate Similarity	NPC96275
0.7362	Intermediate Similarity	NPC313867
0.7362	Intermediate Similarity	NPC322878
0.7362	Intermediate Similarity	NPC316008
0.7356	Intermediate Similarity	NPC315388
0.7333	Intermediate Similarity	NPC470546
0.7317	Intermediate Similarity	NPC314358
0.7312	Intermediate Similarity	NPC109580
0.7312	Intermediate Similarity	NPC64205
0.7312	Intermediate Similarity	NPC6570
0.731	Intermediate Similarity	NPC114806
0.7305	Intermediate Similarity	NPC300443
0.7302	Intermediate Similarity	NPC469443
0.7301	Intermediate Similarity	NPC314388
0.7301	Intermediate Similarity	NPC52748
0.7301	Intermediate Similarity	NPC315283
0.7296	Intermediate Similarity	NPC141050
0.7296	Intermediate Similarity	NPC267237
0.7294	Intermediate Similarity	NPC297145
0.7294	Intermediate Similarity	NPC197743
0.7285	Intermediate Similarity	NPC283760
0.7283	Intermediate Similarity	NPC51047
0.7278	Intermediate Similarity	NPC469903
0.7267	Intermediate Similarity	NPC470545
0.7267	Intermediate Similarity	NPC132636
0.7257	Intermediate Similarity	NPC473000
0.7256	Intermediate Similarity	NPC315266
0.7253	Intermediate Similarity	NPC315542
0.7251	Intermediate Similarity	NPC24617
0.7237	Intermediate Similarity	NPC200964
0.7233	Intermediate Similarity	NPC287401
0.7222	Intermediate Similarity	NPC39822
0.7222	Intermediate Similarity	NPC239762
0.7222	Intermediate Similarity	NPC32064
0.7222	Intermediate Similarity	NPC163392
0.7216	Intermediate Similarity	NPC196091
0.7216	Intermediate Similarity	NPC478005
0.7211	Intermediate Similarity	NPC473450
0.7208	Intermediate Similarity	NPC6975
0.7205	Intermediate Similarity	NPC127741
0.7202	Intermediate Similarity	NPC162104
0.72	Intermediate Similarity	NPC470544
0.7197	Intermediate Similarity	NPC296712
0.7197	Intermediate Similarity	NPC473322
0.7195	Intermediate Similarity	NPC476978
0.7191	Intermediate Similarity	NPC164608
0.719	Intermediate Similarity	NPC71684

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC61004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	382
0.2-0.3	757
0.3-0.4	1807
0.4-0.5	3372
0.5-0.6	2206
0.6-0.7	446
0.7-0.8	41
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD8303	Discontinued
0.8261	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7523	Phase 3
0.7929	Intermediate Similarity	NPD4652	Approved
0.7798	Intermediate Similarity	NPD2098	Approved
0.7785	Intermediate Similarity	NPD7978	Discontinued
0.773	Intermediate Similarity	NPD7303	Discontinued
0.7679	Intermediate Similarity	NPD2097	Approved
0.7677	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8019	Approved
0.7613	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1330	Phase 2
0.761	Intermediate Similarity	NPD7450	Phase 2
0.7562	Intermediate Similarity	NPD8076	Discontinued
0.756	Intermediate Similarity	NPD7495	Discontinued
0.7548	Intermediate Similarity	NPD3136	Phase 2
0.7547	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD8643	Discontinued
0.7425	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7613	Discontinued
0.7377	Intermediate Similarity	NPD7617	Discontinued
0.7371	Intermediate Similarity	NPD5137	Approved
0.7362	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2890	Approved
0.7356	Intermediate Similarity	NPD2888	Approved
0.7356	Intermediate Similarity	NPD2017	Approved
0.7356	Intermediate Similarity	NPD2889	Approved
0.7338	Intermediate Similarity	NPD3125	Approved
0.7329	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7608	Discontinued
0.7289	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6901	Phase 3
0.7262	Intermediate Similarity	NPD7131	Phase 3
0.7257	Intermediate Similarity	NPD7485	Phase 3
0.7257	Intermediate Similarity	NPD7484	Phase 3
0.7244	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8172	Phase 2
0.7205	Intermediate Similarity	NPD8173	Phase 2
0.7191	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8416	Discontinued
0.7188	Intermediate Similarity	NPD6346	Approved
0.7143	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7451	Discontinued
0.7107	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7280	Phase 3
0.7011	Intermediate Similarity	NPD7281	Phase 3
0.7	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7811	Phase 3
0.6979	Remote Similarity	NPD7810	Phase 3
0.6962	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8292	Phase 2
0.6937	Remote Similarity	NPD5263	Approved
0.6905	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6681	Discovery
0.6885	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2561	Approved
0.6879	Remote Similarity	NPD3072	Approved
0.6879	Remote Similarity	NPD3073	Approved
0.6879	Remote Similarity	NPD2562	Approved
0.6879	Remote Similarity	NPD3071	Approved
0.6867	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD9568	Approved
0.6854	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6297	Approved
0.6839	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4125	Approved
0.6826	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2087	Approved
0.6826	Remote Similarity	NPD2088	Approved
0.6824	Remote Similarity	NPD7554	Discontinued
0.6824	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8315	Phase 1
0.6815	Remote Similarity	NPD4762	Approved
0.6815	Remote Similarity	NPD4761	Approved
0.6805	Remote Similarity	NPD1968	Approved
0.6805	Remote Similarity	NPD1967	Approved
0.6805	Remote Similarity	NPD3400	Discontinued
0.6802	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8031	Discontinued
0.6793	Remote Similarity	NPD5485	Approved
0.6793	Remote Similarity	NPD5484	Approved
0.6791	Remote Similarity	NPD6853	Approved
0.6791	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6851	Approved
0.679	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7282	Approved
0.6788	Remote Similarity	NPD6073	Approved
0.6788	Remote Similarity	NPD2568	Approved
0.6772	Remote Similarity	NPD2584	Suspended
0.6768	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5323	Approved
0.6763	Remote Similarity	NPD1670	Discontinued
0.6747	Remote Similarity	NPD3552	Approved
0.6747	Remote Similarity	NPD3554	Approved
0.6747	Remote Similarity	NPD3553	Approved
0.6747	Remote Similarity	NPD3555	Approved
0.6735	Remote Similarity	NPD6256	Approved
0.6735	Remote Similarity	NPD6255	Approved
0.6735	Remote Similarity	NPD6254	Approved
0.673	Remote Similarity	NPD4659	Approved
0.6728	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4676	Approved
0.6727	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5745	Approved
0.6707	Remote Similarity	NPD7086	Phase 2
0.6706	Remote Similarity	NPD6676	Phase 2
0.6687	Remote Similarity	NPD5314	Approved
0.6686	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6253	Approved
0.6667	Remote Similarity	NPD4177	Approved
0.6667	Remote Similarity	NPD4175	Approved
0.6667	Remote Similarity	NPD3040	Approved
0.6667	Remote Similarity	NPD8323	Discontinued
0.6667	Remote Similarity	NPD5445	Approved
0.6667	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5303	Approved
0.6667	Remote Similarity	NPD5304	Approved
0.665	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6836	Approved
0.6647	Remote Similarity	NPD6852	Discontinued
0.6646	Remote Similarity	NPD5299	Approved
0.6646	Remote Similarity	NPD4103	Phase 2
0.6646	Remote Similarity	NPD3055	Approved
0.6646	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3053	Approved
0.6629	Remote Similarity	NPD5773	Approved
0.6629	Remote Similarity	NPD5772	Approved
0.6629	Remote Similarity	NPD7972	Discontinued
0.6628	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2022	Approved
0.6625	Remote Similarity	NPD4677	Discontinued
0.6615	Remote Similarity	NPD6504	Approved
0.6615	Remote Similarity	NPD6505	Approved
0.6613	Remote Similarity	NPD5557	Phase 1
0.6596	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2014	Approved
0.659	Remote Similarity	NPD2013	Approved
0.659	Remote Similarity	NPD2016	Approved
0.6587	Remote Similarity	NPD5725	Approved
0.6587	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5746	Approved
0.6585	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2046	Approved
0.6585	Remote Similarity	NPD2045	Approved
0.6585	Remote Similarity	NPD2044	Approved
0.6585	Remote Similarity	NPD21	Approved
0.6585	Remote Similarity	NPD2047	Approved
0.6585	Remote Similarity	NPD2043	Approved
0.6585	Remote Similarity	NPD2051	Approved
0.6585	Remote Similarity	NPD2048	Approved
0.6584	Remote Similarity	NPD5311	Approved
0.6584	Remote Similarity	NPD5310	Approved
0.6581	Remote Similarity	NPD256	Approved
0.6581	Remote Similarity	NPD255	Approved
0.657	Remote Similarity	NPD5309	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD3059	Approved
0.6566	Remote Similarity	NPD3061	Approved
0.6566	Remote Similarity	NPD3062	Approved
0.6564	Remote Similarity	NPD9569	Approved
0.6559	Remote Similarity	NPD6020	Phase 2
0.6558	Remote Similarity	NPD2229	Approved
0.6558	Remote Similarity	NPD2234	Approved
0.6558	Remote Similarity	NPD2228	Approved
0.6557	Remote Similarity	NPD2517	Approved
0.6556	Remote Similarity	NPD8351	Phase 2
0.6552	Remote Similarity	NPD2874	Phase 2
0.6552	Remote Similarity	NPD3536	Discontinued
0.655	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5027	Approved
0.6543	Remote Similarity	NPD5029	Approved
0.6543	Remote Similarity	NPD5031	Approved
0.6537	Remote Similarity	NPD6189	Approved
0.6537	Remote Similarity	NPD6188	Approved
0.6532	Remote Similarity	NPD4588	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5218	Approved
0.6519	Remote Similarity	NPD5219	Approved
0.6514	Remote Similarity	NPD5229	Approved
0.6514	Remote Similarity	NPD4731	Phase 3
0.6514	Remote Similarity	NPD5230	Approved
0.6514	Remote Similarity	NPD6390	Discontinued
0.6512	Remote Similarity	NPD5481	Discontinued
0.651	Remote Similarity	NPD4435	Approved
0.6509	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5032	Approved
0.6506	Remote Similarity	NPD259	Phase 1
0.6505	Remote Similarity	NPD3909	Discontinued
0.6503	Remote Similarity	NPD2516	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data